8 Years of Freelancing: 8 Things I’ve Learned

Today, I’m celebrating my eighth year of freelancing with cupcakes at The Department, a beautiful 16,000 square foot collaborative workspace in downtown Phoenix. For the past four years, I’ve written a blog post with tips, whining, or reflections. (Here’s 2013, 2014, 2015, and 2016.) So grab a drink and celebrate with me if you’re interested in another round of musings.

You may not need that anchor client.

When I teach courses to new freelancers, or give advice over coffee, I always recommend finding either an anchor client or a part-time job to assure that rent and bills are paid. This helps people avoid the trap of pitching out of desperation or accepting underpaying work. That said, I’ve spent years keeping anchor clients that weren’t ideal out of fear, and when those relationships inevitably ended, I was always able to replace the work. Anchor clients are great for stability, and there are a lot of benefits to having a relationship that doesn’t involve learning a new CMS every month. But if scope creep, boredom, forced positivity, unnecessary meetings, or even unfulfilling work leave you drained, sometimes cutting the cord can be a good thing. It also means you’ll be more agile and able to jump on breaking news almost immediately. I am somewhat risk-averse and wouldn’t trade my ongoing client relationships for the world, but knowing that anchor clients aren’t necessary and not clinging to problematic client relationships has helped me develop more freedom.

It’s okay to just hang out and socialize at conferences.

When I first started freelancing, I’d get up super early to make sure to hit the morning sessions whenever I went to a conference. I’d spend hours figuring out the best tracks, take diligent notes, and sometimes try to sell recaps or summaries. I still judge people who party all night and miss all of the next day’s sessions when there are amazing investigative reporters and industry experts they could be learning from. I still think there’s nothing like soaking up the energy at an in-person panel. But I’ve relaxed my stance a bit over the years. There’s not a lot of time to schmooze with colleagues if you work from home, and I’ve honestly learned just as much partying at hacker conferences as I have taking detailed notes in overcrowded conference rooms. A lot of those talks are available on video a week later, anyway.

You may never feel like you’ve “made it.”

I’ve noticed that no matter what my accomplishments are, I can’t help but feel a little confused when people come to me with amazing projects or stories they want me to break. I have a list of other journalists they could’ve gone to instead. I also get really surprised when people look at me like I’m successful, even though I know that by some external metrics, I am. Being comfortable with the fact that my own view of myself may not align with other people’s, and that the truth is probably somewhere between the two, has helped me navigate this. Just know that a certain byline doesn’t mean people will actually talk to you online or invite you to their parties.

Critics can be your friends.

I used to wonder why people didn’t have anything better to do with their time than blowing up my inbox with minute critiques (which more often than not are mere opinions or end up being inaccurate). Even though sorting through these can be time-consuming and annoying, recognizing that some people think being published makes one authoritative has helped me respond more compassionately. I’ve also learned a lot from concerns and even (gasp!) reading the comments, and it’s helped me improve my writing. No love for trolls, and a lot of PR concerns about so-called “errors” are best ignored, but being thick-skinned and open-minded is definitely beneficial.

Coaching helps.

I used to have what can only be described as an addiction to online courses and communities, even though my ROI was very low. But at the end of last year, I had an in-person annual review and strategy session with Pam Slim, and it has guided my work, mindset, goals, and decisionmaking for all of this year. I just scheduled another session at the end of this year.

Editors are gold (the good ones, anyway)

I started writing back in middle school, for my marching band newsletter and my school paper and a family newsletter and a Star Trek fan club newsletter called the Excalibur Press and my own zines, Apple Crumb, Starlight and Live Beat. I remember reading comic books and zines during free reading time and an unapproving English teacher asking me why I couldn’t ever read something “real.” I was attracted to the raw honesty and creativity in zines like Cometbus, Sanity Sux, Girl Germs, Teenage Gang Debs and in comics like Hate, Eightball, Action Girl, Milk & Cheese, Dork, and Optic Nerve… for the same reason I was attracted to K Records bands like Bratmobile and Bikini Kill and Kicking Giant. I don’t like zines as much as I used to because I feel like some of them could use a little bit of polish. I may just be old and curmudgeonly but I feel like the d.i.y. ethic used to be about becoming the media instead of waiting for approval and acceptance from stodgy establishmentarians. Nowadays, it sometimes seems like people like to put out subpar work out of laziness and call it d.i.y. as an excuse. Perhaps the truth is somewhere in the middle. Too much editing can take the teeth out of good writing. Some editors do little more than adding errors and requiring unnecessary busywork. But not enough editing can lead to work that’s unclear, incomplete, or just not as good as it could be…. and good editors can really make your writing sing. Finding good editors isn’t easy, and I consider myself incredibly lucky that I get to work with so many of them.

Make friends with other journalists and industry experts.

I don’t know what I would do without my friends. I can bounce ideas off of them, give somewhat objective feedback on their challenges, get assistance in rewriting emails so they don’t make people cry, share contacts and intel, and just chat about everything from new tunes to industry news. If you find yourself increasingly isolated, reaching out to others can make your world seem larger.

There are definitely pros and cons.

Freelancing definitely has its perks. The ability to work remotely and set your own schedule. The opportunity to look into whatever you think is interesting at the moment. Experts who can answer your pressing questions just a phone call away. The ability to shine light on injustice to help create a better world. The chance to teach people something that may help them with their lives. Being able provide levity and entertainment in a polarized, toxic world. Getting people to look closer and think deeper. Avoiding unnecessary meetings, if that’s what you want. But freelancing has its downsides. It can be incredibly frustrating, sleazy publications sometimes screw you over, and extroverts like me may miss watercooler talk and getting invited to office parties. There’s really no paid time off, and you have to manage your own retirement savings and health insurance. I haven’t ruled out the possibility of taking full-time work if the opportunity is right, but don’t miss all of the drawbacks of full-time employment either. It’s definitely worth assessing and reassessing to see what’s best for you.